• Home
  • About
    • Meet Cassie
    • Frequently Asked Questions
    • Press
  • Style
    • Date Night
    • Day to Night
    • Dressing Room Diaries
    • Fall & Winter Style
    • Five Ways
    • Now & Later
    • Special Occasion
    • Spring & Summer
    • Style Tips
    • Sugarplum Style
    • Work Wear
  • Travel
    • International
      • Mexico
      • The Bahamas
      • Europe
    • United States
      • Sun
      • Snow
      • Hike
    • Big D
    • Cruising
    • Great Stays
    • Packing Tips
  • Lifestyle
    • Beauty
    • Family
    • Fitness
    • Food
    • Holidays
    • Organizing
    • Parties
    • Personal
    • Ramblings
    • Simple Projects
  • Decor
    • Sugarplum Casa
    • Bathrooms
    • Bedrooms
    • Dining Room
    • Kitchen
    • Laundry & Mudroom
    • Family Room
    • Living Room
    • Tablescapes
    • Outdoor
    • Lake House
    • One Room Challenge
    • Shop My Home
  • shop
    • Gift Guides
    • Monday Mail Day
    • Faves Under $50
    • Amazon Fashion Finds
    • Amazon Home & Decor Finds
    • Look for Less
    • Shop My Instagram
    • Sugarplum Picks
    • My Home
    • My Carry On Bag
  • Contact

Hi Sugarplum!

Sugarplum Style Tip | How to Wear Ankle Boots with Skinny Jeans

December 28, 2017

Happy almost-Friday, friends, and cheers to the long weekend ahead! We have one last (belated) Christmas celebration, and then we’re headed to the lake to usher in the new year with family.

It’s hard to believe another year has come and gone, and I’ve managed to create over 200 posts here! I’ll be recapping all my favorites next week, but thought I’d finish out this year with one of my most-asked style questions this time of year…how do you wear ankle boots with skinny jeans?!

And as is true with most of my Sugarplum Style Tips…my biggest advice is not to overthink it! There really are no rules when it comes to boots and jeans, or how you cuff them. It’s mostly a preference thing. I’ve styled two basic outfits to share my tips, starting with this favorite relaxed cowlneck (currently 40% off!).


Cowlneck Sweater (40% off!) | Jeans | Ankle Booties | Tassel Earrings | Belt | Sunglasses


Cowlneck Sweater (40% off!) | Jeans | Tassel Earrings | Belt | Sunglasses | Cuff Bracelet

And while there are no right or wrong ways for cuffing, some are definitely more flattering than others! When it comes to ankle boots (basically any boot but knee-high or over-the-knee) and skinny jeans, I’m not a fan of tucking your jeans in the boots, or pulling them over the top of the boot. Leave those looks to tall boots and bootcut jeans.

The goal is to see at least a sliver of skin between the boot and hem of the jean.

Depending on the length of your jeans, that likely requires some sort of cuff…and there are several to choose from, depending on the look and style you prefer.

*The Slouchy Cuff*

Most skinny jeans are tight enough to hug the leg, so you can do a single cuff and let the rest of the length scrunch around the ankle. This look is casual and effortless.

*The Wide Cuff*

Fold the excess length up in a single wide cuff, making sure the cuffs are fairly even on both legs. This looks best on tall or leggy girls, as it can visually shorten the legs.

*The Messy Roll*

Fold the jeans up in a single, wide cuff, then fold them up again so the cuff is smaller, but the hem of the jeans are still exposed. This is how I cuff my jeans 99% of the time.

*The Double Roll*

Just as the name suggests, simply fold the hem up twice, creating a clean, even cuff. This style is is a more tailored look.

If you prefer a simpler method, or don’t like to cuff at all, choose jeans with a shorter inseam, or have them altered to ankle-length. Most of my jeans are a shorter inseam like these, and just require a simple, messy cuff.


Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Sunglasses | Leopard Belt | Earrings


Mockneck Sweater (under$50!) | Distressed Jeans | Leopard Belt


Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Leopard Belt

I hope this post was helpful and gave you some fresh ideas for cuffing your jeans with ankle boots. What method do you use most? See more of my Sugarplum Style Tips here.

I hope your holiday has been joyful and merry, and you have a safe, healthy and blessed New Year! I’m so thankful for each of you, and excited to continue this journey together! See you next week for a look back at 2017, and my favorite posts of the year.

Until then, don’t forget about the amazing Half-Yearly Sale at Nordstrom, and the unbelievable prices on a huge selection of in-season staples, including this long cardigan, these buffalo plaid lounge pants, Ugg slippers, and all these booties! Happy New Year, lovebugs!

{Fave Ankle Booties (all on sale!)}


{Huge Sale Alert on These Wardrobe Faves}

 

*Photos by the darling & talented Mary Summers. This post created in collaboration with Nordstrom, but all styling, tips and bowleggedness are my own. Thank you for supporting Hi Sugarplum sponsors!*

 

 


Make sure you follow me on Facebook here for daily sales & sign up for my weekly newsletter here for sneak peeks, special Q&As, & Sugarplum Picks!

by Cassie 
33 Comments
Share:
Fall & Winter Style, Style Tips

 

About Cassie

View all posts by Cassie

Related Posts

  • The new GLxHSP Lounge Set is HERE!
  • Winter Cozies
  • 36 Hours in NYC (+ What I Packed!)
  • Cozy Christmas Style
previous article: 8 Looks for New Years Eve
next article: Best of 2017 | Reader Favorite Buys

Comments

  1. Charmaine Ng | Architecture & Lifestyle Blog says: December 28, 2017 at 4:34 am

    Thank you for the tip! I’ve actually never worn ankle boots with skinny jeans just for the reasons you pictured and mentioned, haha! 🙂

    Charmaine Ng | Architecture & Lifestyle Blog
    http://charmainenyw.com

    Reply
  2. Sandy says: December 28, 2017 at 5:28 am

    Perfect tutorial! Very, very helpful. Like wow on both looks, but the burgundy sweater w/the suede (my weakness-sigh) booties, beyond amazing look. So hip, modern and just plain cool! Killer sales going on right now.
    Your Christmas Crack-oh my GOODNESS! I say, All Year Round Crack-naughty and nice!
    Thanks for enlightening us, Cassie.

    Reply
  3. MELANIE SMITH says: December 28, 2017 at 8:38 am

    Great post!

    Reply
  4. Colleen says: December 28, 2017 at 10:11 am

    This is a great post, thank you. However… I’m in Canada with the windshield today it is -36 Celsius so there is no leg exposure whatsoever. Socks and warm boots are the best fashion accessory with our weather. Stay warm in Texas and take care.

    Reply
    • Cassie says: December 30, 2017 at 11:07 am

      Whoa, that’s cold!! For sure this doesn’t apply to everyone year-round!! I’d be in 18 layers and knee boots in that kind of cold!!!

      Reply
  5. angie ebersole says: December 28, 2017 at 12:33 pm

    Do you wear any low-cut socks ever? I love your look, but my feet don’t do well in just boots.

    Reply
    • Cassie says: December 30, 2017 at 11:06 am

      Sometimes I go without, but usually I wear no-show socks…these are my faves: http://bit.ly/2zvweNy

      Reply
  6. Jennifer says: December 28, 2017 at 3:01 pm

    what if you don’t care for skinny jeans, I’m more of girlfriend jean wearer. how do you wear booties with girlfriend boyfriend jeans?

    Reply
    • Cassie says: December 30, 2017 at 11:06 am

      I would cuff them the exact same!!

      Reply
  7. Jennifer says: December 28, 2017 at 7:43 pm

    So cute. But I have the same question as Angie. Do you wear really low-cut socks, or go without?

    Reply
    • Cassie says: December 30, 2017 at 11:05 am

      Sometimes I go without, but usually I wear no-show socks…these are my faves: http://bit.ly/2zvweNy

      Reply
  8. Ashley says: December 28, 2017 at 11:08 pm

    Love the post, personally I like the double roll look.

    Reply
  9. Sheaffer Sims says: December 29, 2017 at 6:32 am

    Such a wonderful post! I like the messy roll the most!!! Great visuals!

    Reply
  10. Nancy says: December 29, 2017 at 7:07 am

    Must have those gold earrings. Where can I purchase? Love your blog. Happy New Year!

    Reply
    • Cassie says: December 30, 2017 at 11:04 am

      They’re Bauble Bar! http://bit.ly/2zAsxWL

      Reply
  11. Julie says: December 30, 2017 at 8:40 am

    I live in Michigan where it’s been snowing for ten days straight. Yesterday we received 14.7 inches of snow in a 24 hour period. Also did I mention it’s 9 degrees? Skin exposure just isn’t going to happen and I’m not wearing snow boots everyday. While they(the snow boots) are great for outside, they are really not enjoyable inside, and carrying around your boots inside is no fun either. So we tuck, and we will continue to tuck. I guess us northern girls will have to have a big red X on our fashion. Honestly I find the red X kind of offensive. We can’t all live in the south.

    Reply
    • Cassie says: December 30, 2017 at 11:02 am

      I’m sorry you found my post offensive, it certainly wasn’t my intent…it’s just general style advice for a question I get all the time, not cold-weather advice. If I lived in the north, I probably wouldn’t be wearing suede ankle boots! xo. C.

      Reply
      • Julie says: December 30, 2017 at 11:46 am

        No, your post wasn’t offensive, just the red X in a comical sort of way(don’t want to be a fashion don’t)! Sorry if that transpired wrong! We just have no choice but to wear things tucked in/over the outside! Still wear suede in the winter(heels too!), we just treat it with scotch guard and walk carefully! 😉 xoxo

        Reply
        • Julie says: December 30, 2017 at 11:55 am

          …and upon rereading my original comment post it does sound “bitchy”. My intent was not that at all. Sorry! Sometimes when we type we have a smile and a joking manner behind it, and when you go back a reread you realize that was not what came across. Unfortunately you don’t know me and I don’t know you, but if you did you would know that there was no intention of a mean comment.

          Reply
      • Bev says: January 4, 2018 at 8:12 am

        I live in Michigan too and did not find this post one bit offensive! Don’t understand why some feel the need to express negative comments when someone else is just trying to pass along their opinions and helpful advice. I found this useful and have shared it with a couple friends who have also wondered about this. Thank you!

        Reply
  12. Ellen says: December 30, 2017 at 10:37 pm

    I know these are the current fashion “rules” but the look really isn’t flattering on a lot of folks. It makes my legs look very stumpy. Leaving skinnies uncuffed really helps to lengthen my leg line. I like to think we have left the rigid rules behind!

    Reply
    • Cassie says: January 2, 2018 at 3:43 pm

      Definitely no rules…these are just some tips for cuffing and guidelines for people who like them! Fashion is meant to be fun!

      Reply
  13. Shannon says: January 3, 2018 at 1:56 pm

    What size are you wearing in the burgundy mockneck sweater? Thanks!

    Reply
  14. Mimi says: January 3, 2018 at 4:40 pm

    Great post Cassie… Love the skinnie tips with ankle boots! Super helpful…

    Reply
  15. Nichola says: January 5, 2019 at 10:07 pm

    Looks better tucked in with the black boots, because of the dip at the front….if they went straight across then the folded up look would work better.

    Reply
  16. Kerry Mazzacano says: May 4, 2019 at 12:56 pm

    Love the beige boots. Where did you get them?

    Reply
    • Cassie says: May 4, 2019 at 2:38 pm

      Those are several years old from Nordstrom. xo

      Reply
  17. Andraya says: October 8, 2020 at 12:02 pm

    My personal opinion. Looks messy (like rolling up pants that are too Long and you don’t have time to hem). I prefer a more polished tailored classy look. To each his own , You do you.

    Reply
  18. Mose says: October 30, 2020 at 3:36 pm

    I have always tucked my jeans in but leave a slouch. And I’m from the south (some commented on weather). I do have one pair of ankle boots that I don’t tuck because they look funny… I really like to wear crazy socks with some. It all depends on the outfit, my mood, etc. Whatever you think is best, who’s to say you’re wrong? (I started painting my fingernails with one nail a different color YEARS before it became a “thing”!!) But personally, I do think that ankle boots with capris look pretty ridiculous!!

    Reply
  19. V says: November 24, 2020 at 5:10 pm

    Im shocked at how much this helps me. lol. I honestly am just into thigh high boots, or at least knee high, and after purchasing my first legit pair of booties, I felt everything I put on looked so dumb! Thanks for the styling help! <33

    Reply
    • Cassie says: November 25, 2020 at 11:26 am

      Well you are so welcome! I’m thrilled this post is still helpful! xo, Cassie

      Reply
  20. S says: January 7, 2021 at 11:58 am

    Lots of folks in the North wear ankle boots, even when it’s quite cold.You tuck them in, cover the top, or wear socks/tights that cover any showing skin. It isn’t a style faux pas to wear ankle boots and jeans without a cuff. I think you’re just describing a way you like to wear them.

    Reply
    • Cassie says: January 7, 2021 at 12:21 pm

      Hi! I never mean to insinuate that ANYthing is a style faux pas! Of course this is just the way I like to style my ankle boots… in north Texas, we don’t have to worry about it being freezing *that* often! You Northerners have to bundle up! xo, C

      Reply

Leave Your Comments Cancel reply

Your email address will not be published. Required fields are marked *

 

  • Bloglovin
  • Email
  • Facebook
  • Instagram
  • Pinterest
  • RSS
  • Twitter

Don’t Miss a Post

Subscribe to Hi Sugarplum!

Thank you for subscribing!

Archives

  • ►2023 (14)
    • ►February (1)
    • ►January (13)
  • ►2022 (177)
    • ►December (14)
    • ►November (18)
    • ►October (14)
    • ►September (15)
    • ►August (14)
    • ►July (14)
    • ►June (14)
    • ►May (15)
    • ►April (16)
    • ►March (15)
    • ►February (14)
    • ►January (14)
  • ►2021 (201)
    • ►December (19)
    • ►November (20)
    • ►October (18)
    • ►September (13)
    • ►August (14)
    • ►July (15)
    • ►June (17)
    • ►May (18)
    • ►April (17)
    • ►March (17)
    • ►February (15)
    • ►January (18)
  • ►2020 (197)
    • ►December (21)
    • ►November (19)
    • ►October (21)
    • ►September (14)
    • ►August (16)
    • ►July (14)
    • ►June (17)
    • ►May (14)
    • ►April (16)
    • ►March (15)
    • ►February (12)
    • ►January (18)
  • ►2019 (209)
    • ►December (21)
    • ►November (16)
    • ►October (18)
    • ►September (16)
    • ►August (16)
    • ►July (18)
    • ►June (14)
    • ►May (19)
    • ►April (19)
    • ►March (16)
    • ►February (17)
    • ►January (19)
  • ►2018 (207)
    • ►December (18)
    • ►November (20)
    • ►October (19)
    • ►September (14)
    • ►August (17)
    • ►July (16)
    • ►June (16)
    • ►May (20)
    • ►April (17)
    • ►March (16)
    • ►February (16)
    • ►January (18)
  • ►2017 (206)
    • ►December (16)
    • ►November (20)
    • ►October (17)
    • ►September (16)
    • ►August (17)
    • ►July (17)
    • ►June (19)
    • ►May (18)
    • ►April (15)
    • ►March (20)
    • ►February (14)
    • ►January (17)
  • ►2016 (204)
    • ►December (16)
    • ►November (15)
    • ►October (17)
    • ►September (17)
    • ►August (18)
    • ►July (16)
    • ►June (18)
    • ►May (17)
    • ►April (17)
    • ►March (20)
    • ►February (15)
    • ►January (18)
  • ►2015 (203)
    • ►December (17)
    • ►November (16)
    • ►October (18)
    • ►September (16)
    • ►August (16)
    • ►July (18)
    • ►June (15)
    • ►May (16)
    • ►April (17)
    • ►March (17)
    • ►February (17)
    • ►January (20)
  • ►2014 (220)
    • ►December (20)
    • ►November (14)
    • ►October (19)
    • ►September (21)
    • ►August (18)
    • ►July (18)
    • ►June (18)
    • ►May (17)
    • ►April (19)
    • ►March (21)
    • ►February (17)
    • ►January (18)
  • ►2013 (236)
    • ►December (19)
    • ►November (17)
    • ►October (20)
    • ►September (19)
    • ►August (20)
    • ►July (20)
    • ►June (19)
    • ►May (22)
    • ►April (21)
    • ►March (18)
    • ►February (20)
    • ►January (21)
  • ►2012 (248)
    • ►December (21)
    • ►November (19)
    • ►October (23)
    • ►September (21)
    • ►August (21)
    • ►July (20)
    • ►June (18)
    • ►May (21)
    • ►April (20)
    • ►March (22)
    • ►February (21)
    • ►January (21)
  • ►2011 (263)
    • ►December (21)
    • ►November (23)
    • ►October (22)
    • ►September (23)
    • ►August (21)
    • ►July (23)
    • ►June (22)
    • ►May (19)
    • ►April (23)
    • ►March (22)
    • ►February (21)
    • ►January (23)
  • ►2010 (168)
    • ►December (30)
    • ►November (22)
    • ►October (22)
    • ►September (22)
    • ►August (20)
    • ►July (21)
    • ►June (22)
    • ►May (9)

Copyright © 2023 · Hi Sugarplum! · Privacy Policy